双羟基七甲川菁染料的合成及其光谱性能研究

Synthesis and Spectral Properties of Dihydroxy Hematocyanine Dyes

摘要:

论文通过分子设计分别以2,3,3-三甲基吲哚和1,1,2-三甲基-1H-苯并[e]吲哚为原料，首先合成两种季铵盐，再分别同2-氯-1-甲酰-3-羟基亚甲基环己烯缩合，利用Suzuki-Miyaura反应实现染料中位C-C取代，制得四种带有活性羟基的七甲川菁染料。利用核磁和高分辨率质谱对染料结构进行了表征。以乙醇为溶剂，用紫外－可见光谱仪研究了染料的光谱性能：采用电流为13.4A的高压氙灯为灯源，考察了染料的光稳定性；探究了pH值对染料颜色的影响，并尝试推论变色机理。结果表明，四种七甲川菁染料均在近红外区产生较强吸收，在无水乙醇中均具有良好的光稳定性。不同pH值下，染料的光谱性能研究发现，七甲川菁染料吸收光谱受pH影响较大，在pH=5~7之间，染料在近红外区有最佳吸收。

Abstract:

Four heptamethine cyanine dyes with active hydroxyl groups were prepared using 2,3, 3-trimethylindolenine and 1,1, 2-trimethyl-1H-benzo [e] indole as raw materials. Firstly, two kinds of quaternary ammonium salts were synthesized, then they were condensed with 2-chloro-1-formyl-3-hydroxymethyl cyclohexene respectively. Lastly, C-C substitution in dye medium was achieved by Suzuki-Miyaura coupling reaction. The dye structures were characterized by 1HNMR and FTMS spectra;The absorption spectra of four dyes were determined by UV-vis with ethanol as solvent;The high voltage xenon lamp with current of 13.4A was used as the source of the lamp to study the light resistance of the dyes;Investigated the effect of pH value on dye color and deduced the mechanism of color change. The results showed that the four kinds of four heptamethine cyanine dyes have strong absorption in the near infrared region, and have good light stability in anhydrous ethanol. The study on the spectral properties of dyes at different pH values found that the absorption spectrum of four heptamethine cyanine was greatly affected by pH, and the dyes have the best absorption in the near infrared region when the pH value is 5~7.